Yes, get your class A CDL. I think it's well worth the time and money for anyone in construction, excavating, etc, it opens up so many options.
The 26000lb gross weight requirement for a CDL (either straight truck or truck+trailer) is federal. Some states it seems add the more stringent 10000lb trailer requirement, but I personally have never come across that.
It used to be with a 3/4 ton pickup (8500-8800GVWR) or a 1 ton pickup (10000GVWR) you had a lot of trailer choices to still be legal and under CDL. Nowadays the pickup mfg's keep bumping up the GVWR making it difficult to be legal to tow many trailers, despite the trucks having a higher tow rating. My regular cab 2019 F250 has a GVWR of 10K and I think the extended and crew cab versions are 11K+. One tons are getting up into the 14K GVWR now which doesn't leave much room to legally tow a trailer of any weight. I know they keep bumping up the specs to sell more trucks, but I think they are headed in the wrong direction. While I have a class A CDL, I try to keep my pickup + trailer under 26K gross so family, friends, workers can legally drive it if need be, this is getting increasingly harder to do with a 15K trailer.